


Yes, Boss

by teaandchess



Category: Supernatural
Genre: Alternate Universe, Explicit Language, Explicit Sexual Content, F/M
Language: English
Status: Completed
Published: 2013-11-16
Updated: 2013-11-16
Packaged: 2018-01-01 18:31:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,315
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1047194
Author URL: https://archiveofourown.org/users/teaandchess/pseuds/teaandchess
Summary: <blockquote class="userstuff">
              <p>AU: Dean Winchester is getting fed up with his new assistant, who seems to go out of her way to make his life difficult. Meg's just as frustrated that he's not taking the damn hint. (PWP really)</p>
            </blockquote>





	Yes, Boss

      It was all because of his secretary that he was the lone person left on this floor of Winchester PI. Even Sam had stopped in, grinning because his secretary, Ruby, with her 120 word per minute fingers, had booked all his reports out early. No drinks tonight and Dean had been looking forward to hearing that latest on Sam's recent dates with his secretary. The dirty details. Castiel was gone too, not needing a secretary for his work.  
       Though Dean had noticed him making eyes at his latest secretary, Meg Masters. He was even 90% sure that the time he'd caught Castiel in the break room that there had been lipstick the same shade as hers on his mouth. And now, at moments like this he was ready to give her up and let have Cas have her full-time.  
      First time had been an honest mistake, he'd let it slide; then more double bookings happened and he'd actually had a screaming match with her over it. More arguments and some pretty rank insults.  
      Other secretaries flinched.  
      This one smirked and her dark eyes would sparkle as she snarked back at him that maybe he was too dumb to notice his clients were piling up.  
      She was doing it deliberately, his head was saying on repeat lately. Dean just couldn't figure out why.  
      As she sauntered back in, holding a fresh mug of coffee for him, Dean let himself watch her hips twitch under her skirt as she approached. She was a problem; too hot and she knew it. She was too snarky and there was something about this Meg that had sent warning bells off in his head.  
      Too much trouble.  
      “Ms. Masters, you did it again. I was double booked and now I'm four days behind on paperwork because of your incompetence.” Dean stood up and moved around her, loosening his tie as he nudged the door shut. It felt like he was choking on his anger. He was tired and just wanted to go home. He looked at the back of her – fuck what a view because the four inch heels actually made her reach his shoulder and made those slim legs look a mile long- and saw her hands tighten around the mug of coffee. “So what do I do with you?”  
      “With me? Well, Mr. Winchester, I don't think you could ever know what to do with me.” She turned slowly and grinned at him. “But I did come highly recommended.”  
      “You're fucking with me deliberately!” he shouted, losing it because of that knowing grin. “I have work to do and now I'll have to go have dinner with clients to apologize for what you did!”  
      He stepped closer, wanting to see those dark eyes widen in fear. But all she did was smirk and look him up and down. “Dinner? Dressed like that?”  
      Trying to cool his temper – Sam said he yelled at Meg too much lately – he moved closer. “Now, I have to think of what I'm going to do with...”  
      He froze as she took the mug of coffee and poured it down his front. The drink wasn't hot enough to burn but he felt it soak his pants all the same. Meg sucked her lower lip into her mouth and lifted the empty cup between them. Her eyes locked on his, she smirked and let go so the ceramic crashed to the ground.  
      “Oops.”  
      He clenched his teeth, appalled by her behaviour. She had come highly recommended but no one had said she could be such a...  
      “Bitch,” he muttered under his breath, stooping to grab the mug before he tripped on it. As he collected the tiny bits that had shattered, he noticed her moving a little until she was perched on the end of her desk. Her heels swung into his vision as she crossed her legs and he could catch glimpses of pale skin and the lace tops of her thigh highs. Swallowing hard, he tried to ignore the sudden hardening in his cock as he realized that if he angled right he would be so close he could smell her.  
      Ignoring it didn't work. He leaned in a little and thought he could smell the perfume she wore. Before he'd been irritated by the heavy jasmine but now it went straight to his cock and had his head actually feeling fuzzy.  
      Then he smelled something even sexier. Her. It was all female and all sex. He licked his lips, looking up to see her red mouth parted in a smirk.  
      “You know, you could just yell at me some more. Tell me what a bad secretary I've been. Scream at me.”  
      “I could,” he agreed, noticing that her one stiletto was dangling from her toe flirtatiously.  
      “After all, nothing really gets my attention like that does.” Reaching down, she gently lifted the end of his tie and led him forward on his knees. He was so stunned that he could barely think to resist. “You've been yelling at me for weeks now. You haven't figured out that I love the way your voice growls my name?”  
      Thinking back in quick flashes, he suddenly remembered how she'd started making mistakes after that first screaming match. Fuck. He'd forgotten how her tongue would peek out to the side as she thought up some new insult to toss his way.  
       He was the boss, his conscience reminded him. At the very least he shouldn't be on his knees in front of his secretary. Reputation and all that.  
Meg led him forward and spread her legs, the tie still wound around her hand like a lead. Before he could think to move, her legs spread wider and he stared at the shadows of her skirt for a second before looking up.  
      “But maybe... you could just make me scream this time, Mr. Winchester.”  
      All the blood that had been rushing to his brain screaming at him that this was a bad idea went straight to his cock and he felt himself tenting his trousers out. Everything ached and throbbed. Meg's eyes stayed locked on his while one leg lifted over his shoulder, dangling. He could feel the edge of her heel digging into his shoulder blade.  
      “I could,” he repeated. He'd be lying to say he hadn't thought of it. Pretty much a few hours a day were spent ogling her as she leaned down to show him her accounts or trying to ignore the erections that popped up when she brushed around him.  
      Now he was pretty sure she'd been doing it deliberately all this time.  
      He could see the spark of challenge in her eyes and then slow disappointment when he hesitated too long.  
      “But you could just send me home to think about what I've done.” Meg's leg started to slip down and the loss of pressure made him grab hold of her, fingers digging into the tops of her thighs. The soft skin shuddered under his touch and he felt the lace of her stockings bite his fingers when he snagged the calloused tips on them. Her eyes widened just a little as he wrenched her skirt up around her hips as he stood up. He glanced down, noticing her lack of panties, and then back up at her.  
      She was grinning that grin that infuriated him.  
      “I don't think you want that,” he snapped, regaining control fast. His hands pulled again and she went back, sprawled over the edge of his desk with a paperweight digging into her back and a few folders dangling dangerously close to the edge. Folders he'd just organized. He glared at her though the way his palms caressed her spread thighs softened the anger. “Those fall over, you're here overtime.”  
Meg's hair had come out of its prim bun, framing her face and making her look already debauched.  
      “Overtime? Mm.” With a careless flick of her hand, she sent the files toppling to the ground, papers in chaos. Dean watched the last folder fall and took in a deep breath. Meg chuckled and bit her lower lip again, coyly reaching down between them to tug on his belt. “You better make me work for it then.”  
      “Shut it, Masters.”  
      “Make me, boss.”  
      He let her thigh go and dug his fingers into her hair, pulling so hard she grunted in pain as he yanked her up so he could slam his mouth onto hers. Her lipstick tasted bitter but her mouth was soft, yielding a little under his before her tongue slid wet and hot into his mouth. Groaning, he slid his other hand between them, palming at her wet heat when she spread her legs eagerly. As his tongue thrust deep into her mouth, he pushed two fingers into her cunt and found her sopping wet.  
      Ruining his papers probably.  
      Meg's breath escaped out on a whine as he began to curl his fingers forward, his metal watchband grating over her clit. Ripping her mouth away, she hissed and bit at his lower lip. “Fucking Christ.”  
      “You are to have to work hard,” he warned. “Before I let you go home.”  
      “Might want to make a better threat,” she groaned, moving her hips in time with his fingers. He slid them deeper, scissoring his fingers and twisting his wrist to spread her wider. Meg's breath came in gasps and grunts as she tried to get him to move faster. He could feel her cunt actually throbbing around his fingers and Dean grinned, ducking his head and biting at her throat. Sucked at the skin so hard that a deep red bruise formed.  
      “Are you going to come? So fast?” He tried to sound bored, wanting to punish her. But he lost the war when she squirmed and grasped at his shirt, fingers rubbing at his nipples and her tongue peeking out to brush his scruffy jaw. Fuck she was just so wet.  
      “Yeah.” The admission came out soft, her eyebrows furrowed as she strained towards her orgasm. He could feel the greedy clench of her inner walls, feel her getting close. Even her clit was throbbing where he'd wedged his thumb up to tap it.  
      “Mm. I don't think so.” Ignoring the ache in his own cock, he yanked back and his fingers slid out of her with a wet sound. Meg was panting for breath, her eyes wide and furious when they snapped open. She slid off the desk and started for him.  
      “You piece of...”  
      “You don't deserve a reward like that when you've done such bad work. You're the worst secretary I've had yet,” he said before she could get further. Knowing what it could do to her, he popped his shiny wet fingers into his mouth and sucked slowly. Meg's eyes were on his mouth and he popped the fingers back out to point at the coffee cup he'd left on the floor and the files. “So fix this mess up and then we'll talk.”  
      Her anger was so hot that he could feel it burning off her as she passed him. Dean watched her from the corner of his eye as he took a seat in his comfy leather chair. She fixed the folders on a side table and tossed the coffee cup in the trash, the entire time bending over with her skirt still hiked over her hips and her mussed hair dangling around her face. Grinning, he folded his hands in front of him and waited. Tried to ignore the way his erection was throbbing angrily at him stopping. Still...  
      It felt good to have caught her off guard.  
      At least, he thought he had until she turned back around and began to slowly unbutton her blouse. Swallowing down the lump in his throat and subtly trying to control the urge to throw her down, he watched her shrug one shoulder, then the other out of her white blouse to reveal a deep red bra that pushed her breasts up towards him.  
      Inviting him, he was pretty sure.  
      “How was that?” she asked, casually tossing her shirt over to him. It landed on his head and he breathed in the perfume before he pulled it back down. When his eyes opened she was standing in front of him, squeezed between him and the desk. He was pretty sure if the janitor walked in he'd have a heart attack. Dean wouldn't be too far behind him with the way his heart stopped for a second.  
      “Sexy.”  
      “I was going for 'good work, Meg', but that'll do.” She knelt down on the chair, nudging his legs apart so she could lean into him. Running her nose over his cheek, she dragged her tongue over his lips and he parted them. “You could yell at me some more.”  
      “I think you deserve for me to be nice,” he hissed and his hands grabbed her hips, yanking her down so that she was rubbing against his cock. Meg groaned and rubbed against him, canting her hips in a tight thrust so he pushed up at her. Her lips wrapped around his earlobe and she bit hard as she reached between them and undid his belt. Her hands felt soft but strong as they pulled his cock out of his boxers and let the wet skin meet the air conditioned breeze. He hissed as she rubbed the head of his cock against her upper thigh and pushed on the tip a little, smearing precome over him.  
      “You can be bossy if you want to be.”  
_Fuck... this girl._  
      It was a haze, he was barely sure who put a condom on him or how Meg knew he kept a few in his desk drawer. He kept his eyes on Meg's face as she licked her lips and stared at the slow slide of latex over him. As if it was the sexiest thing she'd ever seen. He was sure he'd never been so ready to come just from a pair of hands smoothing a condom down over him. Arching his back, he groaned and rocked a little. Wanting more pressure, more strokes.  
      Meg made her own soft sound, rubbing her cunt against his thigh so that he could feel each wet drag through his trousers as she continued to stroke him. Her head was thrown back and she ground herself down harder and harder, until the force of it made his eyes open so he could watch her.       Reaching out, he yanked her bra down so her nipples were exposed, hard and tight. Her eyes opened and she groaned, straddling his hips again and lifting a breast with one hand.  
      “Come on, baby,” she said, rubbing herself against his cock. “Gonna teach me a lesson?”  
      The taunt should have made him angry but he lost that feeling as he sucked her nipple into his mouth hard and heard her squeal when he bit down. Not able to take it, he wrapped his arm around her waist and pulled her up and then down, thrusting deep into her. The heat enveloping him made him groan and her nipple fell out of his mouth as he leaned in and licked at the sweat on her collarbone. Meg groaned and rocked her hips back up at him, nails digging into his shoulders.  
      The leather chair squeaked and rolled a bit as she fucked herself on his cock and he let his head fall back a bit, loving how she bit and sucked at his neck next. Meg's moans were higher pitched than he dreamt, needy and breathless one moment, dark and growling the next.  
She was just so wet that he felt like he could happily drown in her body. His cock twitched and throbbed, hungry for more as she circled and rocked her hips against his. “Come on,” he said, peeking an eye open. “I can put a better mark on your PA if you try.”  
      She chuckled, sweat coating her pale body and making her hair cling to her skin, and opened her eyes.  
      “Yes, boss.”  
      Leaning forward, she took his lower lip in her mouth as she stroked her hands down his abdomen, nails digging into his skin. Dean hissed, not ready for the pain and the pleasure of that, and Meg bit harder into his lip as she reached between them to stroke at herself. The sight of her chasing her own pleasure, at the wet mess they were making of his expensive chair, made the arm around her waist tighten so he could thrust harder up into her. Knowing they could fall off the chair, he lifted her up and stood for just two seconds before he slammed her onto the desk beneath him.  
Meg moaned, legs going up on his shoulders as she held onto his tie and pulled him down onto her so he could thrust harder. Dean bit at her calf muscle and closed his eyes, feeling her fingers brushing his cock as she rubbed at her own clit. She was crying out and moaning alternatively, letting him know how close she was as her cunt throbbed and clenched around him.  
      “Fuck!” she shouted, her scream in his ear following making his head spin. Her body shook as she came, legs squeezing around his neck a little and he felt her inner muscles flutter and -fuck- squeeze as she bore down on him. Not wanting to stop, he moved harder and faster, until her head banged the edge of the desk and he had to grip the wood to keep from sliding with her across it. Licking his thumb, he slid it between them and squeezed and pinched at her clit.  
      The pain got her off again, the second orgasm right on the edge of the first and he felt everything about her soften just as her cunt clenched hard around his cock again. Too much, his head actually went blank as he felt his orgasm washed over him.  
      “Fuck fuck fuck,” he groaned, thrusting harder and harder to try to drag it out as it pulsed through him. Meg's hold on his tie was near choking him now but he liked how breathless it made him. Still jerking, he dropped on top of her and let his hips twitch and roll into hers.  
      Meg hummed in pleasure at the sensation and he felt her rock up into him, wanting more. He could barely breathe now as exhaustion went through him.  
      Fuck... maybe this was why he had hired her. Besides her sass and her way of challenging him, this woman was unbelievable.  
      He could barely prop himself up over her and catching her knowing smirk made his cock, unbelievably, twitch again. He wasn't even sure what to say.       He didn't fuck his secretaries. He wasn't Sam after all.  
      Well, you fuck them now, that evil voice in his head groaned.  
      “Mind if I come in early tomorrow?” Meg asked unexpectedly and he blinked. He'd been sure she was going to say something... well... romantic, girly, or even something to try to make this more than a fuck on his desk. She grinned devilishly. “I'd really love to go over that new case with you, Mr. Winchester. We can go over the case details.”  
      Her cunt actually clenched around his softening cock and he moaned a little. “Over and over again,” Meg finished, “Until I have it just right for you.”  
      Dean saw the slant to her smeared red lips and knew she was trying to get one over him. He grinned back, recovering as fast as he could went he could still smell sex and sweat all around them, still taste her on his tongue.  
      “What makes you think you are leaving early tonight? We still have work to do.”  
      Meg arched a brow and smiled. “Yes, boss.”


End file.
